Start-ups and Stupid Stuff

By Barry Maher

August 22, 2025 5 min read

"I'm going to make you a billionaire," Benito Mussolini said. That would certainly come in handy. He'd read one of my marketing books. Since Bill Gates contributed a chapter, Mussolini probably thought we were pals. Bill Gates wouldn't know me if I broke into his house — which I might have considered, given the royalties from that particular book. Still, I quickly turned him down — Benito Mussolini, not Bill Gates. If Bill Gates offered to make me a billionaire, I'd listen for as long as he wanted to talk. So, if you happen to read this, Bill ...

But Benito Mussolini (not his real name, just a pseudonym I can remember) kept calling, trying to get me to join his start-up. He kept upping his offer, claiming significant corporate backing. His plan was to help companies of all sizes advertise on the Internet. But just how he would do that seemed different every time he explained it. Sometimes a little different. sometimes a lot.

Still, I was between books, just getting started as a speaker, doing what a friend called S.D.S.S. consulting. It was lucrative — charge a lot and they figure you must be good. A business would bring me in, and I'd work up a lengthy report on them, basically saying, "Stop doing stupid stuff." They'd agree with virtually everything, implement none of it, and a year or two later, they might hire me again to tell them the same things. The stupid stuff market is unlimited.

So eventually Benito and I settled on a deal. Nice salary, a piece of the business, a generous advance — and the check cleared. I got myself a place in L.A., two miles — an hour drive — from his headquarters. He wanted me to move in with him on the beach in Malibu, but fanatics, even genial ones, are about as much fun as ... well, Benito Mussolini.

I soon discovered this Benito was devoted to start-up chic. He did everything but pin up CEO photos from Fast Company. He'd renovated a decrepit old warehouse. Filled it with the latest start-up furniture, top-of-the-line computers, ping pong tables and enough snacks to feed Somalia. The espresso machine was so complex, two of the engineers couldn't start it. I was terrified of blowing it up and putting a giant hole in a new wall or my old self.

Benito hired a noted commercial artist — "she's so expensive, she must be good" — to design a logo. He put it on everything in sight. Including a giant rooftop sign probably visible from Chicago, and for some weird reason, a hundred and fifty baseball shirts and caps. There were nine of us, 12 at our height.

Meanwhile, the software we were working towards never got finalized enough to be usable. Benito was completely dedicated, completely sincere and completely out of his mind. He was an innovator who couldn't stop innovating with a constant flow of random ideas picked up from people at his gym, people in bars, occasionally from dreams and at least once from a seance. Despite our top-flight technical team, little was ever accomplished. Most of what they worked on became obsolete before it was finished.

Years later, I ran into an executive from our corporate sponsor. Apparently, just before they'd let us go belly up, they'd made Benito an offer. They'd buy us using their stock as long as Benito agreed to be replaced by their choice of CEO. Benito turned them down. Playing CEO was more important to him than getting rich.

Later, I checked, and in an old file cabinet, I still had a folder on the start-up. I could easily figure out my ownership percentage, calculate how many corporate shares I would have received, and look up their current value. I tossed the folder — unopened — into the trash. Could Benito have made me a billionaire? Probably not. I certainly could have been rich. But wasting time thinking about it now would definitely be stupid stuff.

Barry Maher is the author of the suspense/horror novel, The Great Dick: And the Dysfunctional Demon. Suggest stories or sign up for the Slightly Off-Kilter newsletter at www.barrymaher.com.

To find out more about Barry Maher and read features by other Creators Syndicate writers and cartoonists, visit the Creators Syndicate website at www.creators.com.

Photo credit: Alexander Grey at Unsplash

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